Hydrazine hydrate (1:1) → 3-Hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

HRID 1890939Notes

Reaction equation

HRID 1890939 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:6][CH:7]=1.O.[NH2:15][NH2:16]>C(O)C>[CH3:13][N:11]1[CH:12]=[C:8]([C:5]2[N:4]=[N:3][C:2]([NH:15][NH2:16])=[CH:7][CH:6]=2)[CH:9]=[N:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 545956073-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Product 1

HCID 580751723-Hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)pyridazineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-chloro-6-(1-methyl-1H-pyrazole-4-yl)-pyridazine (21.0 g, 108 mmol) in ethanol (370 mL) was added hydrazine monohydrate (36 mL). The reaction mixture was stirred at reflux for 18 h, then cooled to room temperature. The precipitate was collected via filtration, washed with cold ethanol and dried in vacuo to provide 18 g of [6-(1-methyl-1H-pyrazol-4-yl)-pyridazin-3-yl]-hydrazine as a beige solid (87% yield): 1H NMR (DMSO-d6) δ 3.88 (s, 3H), 4.28 (s, 2H), 7.02 (d, 1H), 7.59 (d, 1H), 7.83 (s, 1H), 7.91 (s, 1H), 8.19 (s, 1H); MS (m/z) 191 [M+H+]+.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationThe precipitate was collected via filtration
  3. washwashed with cold ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-cc681e5843e44b7abb902fe254c9feef
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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